Organocatalysis in Ionic Liquids: Highly Efficient L-Proline-Catalyzed Direct Asymmetric Mannich Reactions Involving Ketone and Aldehyde Nucleophiles

Synlett

Volumn , Issue 12, 2003, Pages 1906-1909

  Chowdari, Naidu S ^a   Ramachary, D B ^a   Barbas III, Carlos F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Enamine; Green chemistry; Ionic liquids; Mannich reaction; Proline

Indexed keywords

ALDEHYDE DERIVATIVE; ALPHA IMINOETHYLGLYOXYLATE; AMINO ACID DERIVATIVE; GLYOXYLIC ACID DERIVATIVE; IMINE; ION; KETONE DERIVATIVE; PROLINE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL COMPOSITION; ENANTIOSELECTIVITY; ISOLATION PROCEDURE; LIQUID; MANNICH REACTION; REACTION ANALYSIS; RECYCLING;

EID: 0142091320     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41483     Document Type: Article

References (39)

1. (a) Mannich, C.; Krosche, W. Arch. Pharm. 1912, 250, 647.
2. (b) Kleinmann, E. F. Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergmon Press: New York, 1991, Chap. 4.1.
3. (c) Williams, R. M.; Hendrix, J. A. Chem. Rev. 1992, 92, 889.
4. (a) Yamasaki, S.; Iida, T.; Shibasaki, M. Tetrahedron 1999, 55, 8857.
5. (b) Juhl, K.; Gathergood, N.; Jorgensen, K. A. Angew. Chem. Int. Ed. 2001, 40, 2995.
6. (c) Notz, W.; Sakthivel, K.; Bui, T.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 199.
7. Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F. III J. Am. Chem. Soc. 2002, 124, 1842.
8. (e) List, B. J. Am. Chem. Soc. 2000, 722, 9336.
9. (f) List, B.; Pojarliev, P.; Beller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
10. (a) Córdova, A.; Watanabe, S.-I.; Tanaka, F.; Notz, W.; Barbas, C. F. III J. Am. Chem. Soc. 2002, 124, 1866.
11. (b) Córdova, A.; Barbas, C. F. III Tetrahedron Lett. 2002, 43, 7749.
12. (c) Watanabe, S.-I.; Córdova, A.; Tanaka, F.; Barbas, C. F. III Org. Lett. 2002, 4, 4519.
13. (d) Córdova, A.; Barbas, C. F. III Tetrahedron Lett. 2003, 44, 1923.
14. (a) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275.
15. (b) Song, C. E.; Lee, S.-G. Chem. Rev. 2002, 102, 3495.
16. Zhong, G.; Hoffmann, T.; Lerner, R. A.; Danishefsky, S.; Barbas, C. F. III J. Am. Chem. Soc. 1997, 119, 8131.
17. (a) List, B.; Lerner, R. A.; Barbas, C. F. III J. Am. Chem. Soc. 2000, 122, 2395.
18. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F. J. Am. Chem. Soc. 2001, 123, 5260.
19. (c) Cordova, A.; Notz, W.; Barbas, C. F. III. J. Org. Chem. 2002, 67, 301.
20. (d) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas, C. F. III Tetrahedron Lett. 2002, 43, 9591.
21. (e) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F. III Tetrahedron Lett. 2001, 42, 4441.
22. (f) Betancort, J. M.; Barbas, C. F. III Org. Lett. 2001, 3, 3737.
23. (g) Thayumanavan, R.; Ramachary, D. B.; Sakthivel, K.; Tanaka, F.; Barbas, C. F. III Tetrahedron Lett. 2002, 43, 3817.
24. (h) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F. III Tetrahedron Lett. 2002, 43, 6743.
25. (i) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F. III Org. Lett. 2003, 5, 1685.
26. 2e,f and following references: Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798.
27. (k) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458.
28. (l) Bogevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem. Int. Ed. 2002, 41, 1790.
29. (m) Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 8331.
30. (n) Enders, D.; Seki, A. Synlett 2002, 26.
31. (o) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167.
32. (a) Welton, T. Chem. Rev. 1999, 99, 2071.
33. (b) Wasserscheid, P.; Keim, W. Angew. Chem. Int. Ed. 2000, 39, 3772.
34. (c) Sheldon, R. A. Chem. Commun. 2001, 2399.
35. 2O extracts were concentrated to obtain the Mannich product. The ionic liquid containing L-proline was dried under vacuum prior to reuse.
36. 2O (4 x 5 mL). The combined ether extracts were concentrated and chromatographed to obtain the Mannich product.
37. Hoffmann, T.; Zhong, G.; List, B.; Shabat, D.; Anderson, J.; Gramatikova, S.; Lerner, R. A.; Barbas, C. F. III J. Am. Chem. Soc. 1998, 120, 2768.
38. (a) Loh, T. P.; Feng, L. C.; Yang, H. Y.; Yang, J. Y. Tetrahedron Lett. 2002, 43, 8741.
39. (b) Kotrusz, P.; Kmentova, I.; Gotov, B.; Toma, S.; Solcaniova, E. Chem. Commun. 2002, 2510.